Patent GB-867842-A (GB)
Title: Rosin products and their use in coating gelatin compositions
IPC: G03C1/38
Filed: 1957-07-30
Abstract: A method of preparing a rosin product comprises reacting a rosin material, as defined, with an isocyanato carboxylic acid ester so as to form a -CONH link.  Rosin material is defined as rosin acids containing rosinyl, hydrorosinyl and dehydrorosinyl groups, derivatives of these rosin acids such as maleo-pimaric acid, rosin amines, rosin alcohols, hydrogenated and dehydrogenated derivatives of these amines and alcohols and polyethoxy derivatives of the rosin acids, amines and alcohols and of the hydrogenated and dehydrogenated derivatives of the amines and alcohols.  The invention includes compounds of the formula: R11-X-CO.NH.CH(R1)COOH or R11.CO.NH.CH(R1)COOH and their water soluble salts where R11 is a rosinyl, hydrorosinyl or dehydrorosinyl radical, X is CH2O, CH2NH or CH2O(CH2CH2O)n where n has a value from 1-10 or R11CO is a maleo-pimaroyl radical, and R1 is H, an alkyl group having less than 5 carbon atoms or (CH2)mCOOH where m=0, 1, 2, or 3.  The compounds may be prepared for example, by reacting an ester of the formula OCN.CH (R1)COOR, where R is an alkyl group containing up to 3 carbon atoms with a rosin acid to give an amide, a rosin amine to give a urea, a rosin alcohol to give a urethane and a polyoxyethylene derivative of a rosin alcohol, formed by treating the alcohol with ethylene oxide, to give a urethane.  The reaction may be carried out by heating approximately equivalent amounts of ester and rosin compound in a solvent such as chlorobenzene and hydrolysing the ester groups of the product which may be isolated for example, as the sodium salt.  Mixtures of compounds may be obtained by using mixtures of rosin compounds in the reaction. Amides may be prepared using a rosin compound such as abietic acid, dihydroabietic acid, tetrahydroabietic acid or dehydroabietic acid.  Maleopimaric acid, the Diels-Alder adduct of laevopimaric acid and maleic acid, may also be used to prepare amides.  Ureas may be prepared using " Rosin Amine D ", a primary amine with the C12H27 residue of dehydroabietic acid. Urethanes may be prepared using " Abitol ", a mixture of primary alcohols having the C19 residue of abietic, dihydro, tetra hydro and dehydro abietic acids or polyoxyethylene derivatives of the " Abitol " alcohols.  The esters used in the process may be derived from mono- or di-carboxylic acids and the isocyanato esters of acetic, propionic, isovaleric, succinic and glutaric acids are mentioned.  In the Examples (1) " sodium rosinoyl aspartate " is prepared using a mixture of rosin acids and diethyl isocyanato succinate, the ester groups being hydrolysed with sodium hydroxide; (2) " tetrasodium maleopimaroyl aspartate " is prepared using maleopimaric acid (obtained from gum oleoresin and maleic anhydride) and diethyl isocyanato succinate; (3) N-(a ,b -dicarboxyethyl)-N1-(3-isopropyl-7: 10a-dimethyl - 5:6:6a:7:8:9:10:10aoctahydrophenanthryl) urea as its disodium salt is prepared using " Rosin Amine D " and dimethyl isocyanato succinate; (4) " sodium N-abityloxycarbonyl glutamate " is prepared using " Abitol " and dimethyl a -isocyanato-glutarate; (5) " sodium-N-abityl oxy-carbonyl polyethoxy glucine " is prepared using the polyoxyethylene derivatives of " Abitol " and ethyl isocyanato acetate.  The compounds may be incorporated in a gelatin composition to facilitate coating the gelatin on a support.  Specifications 716,080 and 834,525 are referred to.